Friends may not do what you need them to do.
Friends may not know what they CAN do, so they overinflate their value.
Friends may take liberties that strangers wouldn’t.
Friends may not work as hard as strangers.
Friends may not listen.

Despite these potential drawbacks, Kownacki offers some advice based on his own successful collaboration with friends, including knowing when the bend and keeping the communications channels open. And he points out the benefits to having friends as co-workers, not least of which is having a sympathetic ear handy when things get tough (as they do all too often in this crazy web worker economy of ours).

Given the amount of recruiting that goes on in coffeehouses and chatrooms these days, it’s almost impossible to avoid working with friends. But just because you’re basking in the glow of shared hopes now doesn’t mean that you shouldn’t plan for an uncertain future. If you’d like some more practical advice, consider these tips as a starting point:

Think it through. Ask yourself the simple question: would you want to work with this person if they weren’t already your friend? If they don’t have the right skills for the job, then this isn’t a good idea, no matter what fun you have together at the bowling alley or the beach.

Put it in writing. Sure, everyone is happy and great buddies now. But money really does change everything, whether it’s the riches of success or the ugly repercussions of bankruptcy. If your friendship won’t withstand a trip to the lawyer to figure out how to formalize your partnership, maybe this isn’t such a good idea in the first place.

Leave some breathing room. Just how close are you? Will a friendship that’s been good for a few hours a week in bars handle forty or fifty hours a week crunching on code or design comps? Even married couples need some time apart. Think about how much time you really want to spend together. Web workers may have an advantage here in that we tend to build our work weeks out of a number of shifting alliances in the first place.

Sleep on it. Business is risky. I’ve seen several friendships ruined forever by business risks that turned out wrong. If you’re not willing to lose the friend, don’t go into business with them. You might be the lucky one, but the only sure way to win that game is not to play.

Have you gone into business with friends? Did it work out? Or do you have some juicy horror stories to share with your web-working peers? Here’s your chance to spill the beans!